57805-35-3Relevant academic research and scientific papers
Base-Promoted Synthesis of Polysubstituted 4-Aminoquinolines from Ynones and 2-Aminobenzonitriles under Transition-Metal-Free Conditions
Kumar, Ankit,Mishra, Pawan K.,Saini, Kapil Mohan,Verma, Akhilesh K.
supporting information, p. 2546 - 2551 (2021/03/16)
A transition-metal-free and base-promoted one-pot reaction of ynones with 2-aminobenzonitriles is described. The reaction was initiated through sequential aza-Michael addition/intramolecular annulation to afford various multisubstituted 4-aminoquinolines
Regio- and Stereoselective Hydrosulfonylation of Electron-Deficient Alkynes: Access to Both E- and Z-β-Sulfonyl-α,β-Unsaturated Carbonyl Compounds
Zhang, Wei,Johnson, Gabriel M.,Guan, Zhi,He, Yan-Hong
supporting information, p. 4562 - 4570 (2018/10/24)
A metal-free hydrosulfonylation of electron-deficient alkynes with sodium sulfinates or sulfinic acids to access both E- and Z-β-sulfonyl-α,β-unsaturated carbonyl compounds has been developed. We propose that this reaction via a hydroxylallene intermediate delivers the thermodynamically stable E isomer, or via a concerted termolecular AdE3 mechanism affords Z isomer. The stereoselectivity of addition (syn or anti) can be controlled by varying the sulfonyl sources and acidic buffer solutions. This protocol exhibits broad substrate scope for internal or terminal alkynes including various substituted ynones and alkynyl esters. This approach is mild, efficient, operationally simple and easy to be scaled-up. (Figure presented.).
Dual Hypervalent Iodine(III) Reagents and Photoredox Catalysis Enable Decarboxylative Ynonylation under Mild Conditions
Huang, Hanchu,Zhang, Guojin,Chen, Yiyun
supporting information, p. 7872 - 7876 (2015/06/30)
A combination of hypervalent iodine(III) reagents (HIR) and photoredox catalysis with visible light has enabled chemoselective decarboxylative ynonylation to construct ynones, ynamides, and ynoates. This ynonylation occurs effectively under mild reaction conditions at room temperature and on substrates with various sensitive and reactive functional groups. The reaction represents the first HIR/photoredox dual catalysis to form acyl radicals from α-ketoacids, followed by an unprecedented acyl radical addition to HIR-bound alkynes. Its efficient construction of an mGlu5 receptor inhibitor under neutral aqueous conditions suggests future visible-light-induced biological applications.
Zinc-Catalyzed Dehydrogenative Cross-Coupling of Terminal Alkynes with Aldehydes: Access to Ynones
Tang, Shan,Zeng, Li,Liu, Yichang,Lei, Aiwen
supporting information, p. 15850 - 15853 (2016/01/29)
Because of the lack of redox ability, zinc has seldom been used as a catalyst in dehydrogenative cross-coupling reactions. Herein, a novel zinc-catalyzed dehydrogenative C(sp2)-H/C(sp)-H cross-coupling of terminal alkynes with aldehydes was dev
Privilege Ynone Synthesis via Palladium-Catalyzed Alkynylation of "Super-Active Esters"
Yu, Bo,Sun, Huaming,Xie, Zunyuan,Zhang, Guofang,Xu, Li-Wen,Zhang, Weiqiang,Gao, Ziwei
supporting information, p. 3298 - 3301 (2015/07/15)
A neat palladium-catalyzed alkynylation reaction was developed with "super-active ester" as the carbonyl electrophile, which provides a clean and efficient synthetic protocol for a broad array of ynone compounds under CO-, Cu-, ligand-, and base-free conditions. The superior activity of triazine ester was rationalized by the strong electron-withdrawing ability and the unique affinity of triazine on palladium. A mechanistic experiment clearly demonstrated that the N-Pd coordination of triazine plays a crucial role for the highly efficient C-O activation. (Chemical Equation presented).
Simple and efficient one-pot, three-component, solvent-free synthesis of β-enaminones via sonogashira coupling-michael addition sequences
Palimkar, Sanjay S.,More, Vijaykumar S.,Srinivasan, Kumar V.
, p. 1456 - 1469 (2008/09/21)
A simple, efficient, and environmentally friendly one-pot, three-component synthesis of β-enaminones via Sonogashira coupling-Michael addition sequences under solvent-free conditions has been reported. Also the synthesis of β-enaminones has been achieved
